The first radiosynthesis of [11C]AZD8931 as a new potential PET agent for imaging of EGFR, HER2 and HER3 signaling

Bioorganic and Medicinal Chemistry Letters

Volumn 24, Issue 18, 2014, Pages 4455-4459

  Wang, Min ^a   Gao, Mingzhang ^a   Zheng, Qi Huang ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

Cancer; Epidermal growth factor receptor (EGFR ErbB HER); lzheimer's disease; Positron emission tomography (PET); Radiosynthesis; 11C AZD8931

Indexed keywords

ACETAMIDE DERIVATIVE; EPIDERMAL GROWTH FACTOR RECEPTOR; EPIDERMAL GROWTH FACTOR RECEPTOR 2; EPIDERMAL GROWTH FACTOR RECEPTOR 3; N DESMETHYL [2 [4 [[4 [(3 CHLORO 2 FLUOROPHENYL)AMINO] 7 METHOXYQUINAZOLIN 6 YL]OXY]PIPERIDIN 1 YL]ACETAMIDE]; N METHYLACETAMIDE; NITROBENZOIC ACID DERIVATIVE; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG; [2 [4 [[4 [(3 CHLORO 2 FLUOROPHENYL)AMINO] 7 METHOXYQUINAZOLIN 6 YL]OXY]PIPERIDIN 1 YL]N METHYLACETAMIDE] C 11; AZD 8931; CARBON; EGFR PROTEIN, HUMAN; ERBB2 PROTEIN, HUMAN; ERBB3 PROTEIN, HUMAN; QUINAZOLINE DERIVATIVE;

ARTICLE; DRUG ISOLATION; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; POSITRON EMISSION TOMOGRAPHY; PRECURSOR; RADIOCHEMISTRY; SOLID PHASE EXTRACTION; CHEMISTRY; DIAGNOSTIC USE; HUMAN; METABOLISM; SIGNAL TRANSDUCTION; SYNTHESIS;

CARBON RADIOISOTOPES; HUMANS; POSITRON-EMISSION TOMOGRAPHY; QUINAZOLINES; RECEPTOR, EPIDERMAL GROWTH FACTOR; RECEPTOR, ERBB-2; RECEPTOR, ERBB-3; SIGNAL TRANSDUCTION;

EID: 84906966958     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2014.07.092     Document Type: Article

References (39)

1. Z. Cai, H. Zhang, J. Liu, A. Berezov, R. Murali, Q. Wang, and M.I. Greene Semin. Cell Dev. Biol. 21 2010 961
2. H. Zhang, A. Berezov, Q. Wang, G. Zhang, J. Drebin, R. Murali, and M.I. Greene J. Clin. Invest. 117 2007 2051
3. C.L. Arteaga, and J.A. Engelman Cancer Cell 15 2014 282
4. E.M. Bublil, and Y. Yarden Curr. Opin. Cell Biol. 19 2007 124
5. H.S. Cho, and D.J. Leahy Science 297 2002 1330
6. P.M. Mitrasinovic Curr. Drug Targets 14 2013 817
7. P. Warnault, A. Yasri, M. Coisy-Quivy, G. Cheve, C. Bories, B. Fauvel, and R. Benhida Curr. Med. Chem. 20 2013 2043
8. Z. Mu, T. Klinowska, X. Dong, E. Foster, C. Womack, S.V. Fernandez, and M. Cristofanilli J. Exp. Clin. Cancer Res. 33 2014 47
9. B. Barlaam, J. Anderton, P. Ballard, R.H. Bradbury, L.F.A. Hennequin, D.M. Hickinson, J.G. Kettle, G. Kirk, T. Klinowska, C.L. Brempt, C. Trigwell, J. Vincent, and D. Ogilvie ACS Med. Chem. Lett. 4 2013 742
10. D.M. Hickinson, T. Klinowska, G. Speake, J. Vincent, C. Trigwell, J. Anderton, S. Beck, G. Marshall, S. Davenport, R. Callis, E. Mills, K. Grosios, P. Smith, B. Barlaam, R.W. Wilkinson, and D. Ogilvie Clin. Cancer Res. 16 2010 1159
11. P. Ballard, H.C. Swaisland, M.D. Malone, S. Sarda, S. Ghiorghiu, and D. Wilbraham Xenobiotica 2014 Jul 9:1-6. [Epub ahead of print]
12. S. Tjuandin, V. Moiseyenko, V. Semiglazov, G. Manikhas, M. Learoyd, A. Saunders, M. Stuart, and U. Keilholz Invest. New Drugs 32 2014 145
13. T. Kurata, J. Tsurutani, Y. Fujisaka, W. Okamoto, H. Hayashi, H. Kawakami, E. Shin, N. Hayashi, and K. Nakagawa Invest. New Drugs 2014 May 31. [Epub ahead of print]
14. G. Morrison, X. Fu, M. Shea, S. Nanda, M. Giuliano, T. Wang, T. Klinowska, C.K. Osborne, M.F. Rimawi, and R. Schiff Breast Cancer Res. Treat. 144 2014 263
15. J.-Q. Wang, M. Gao, K.D. Miller, G.W. Sledge, and Q.-H. Zheng Bioorg. Med. Chem. Lett. 16 2006 4102
16. M. Gao, C.M. Lola, M. Wang, K.D. Miller, G.W. Sledge, and Q.-H. Zheng Bioorg. Med. Chem. Lett. 21 2011 3222
17. H.S. Ban, Y. Tanaka, W. Nabeyama, M. Hatori, and H. Nakamura Bioorg. Med. Chem. 18 2010 870
18. Y. Chen, M. Feng, S. Li, J. Xu, H. Ning, Y. He, X. Wang, R. Ding, and C. Qi Bioorg. Med. Chem. Lett. 22 2012 4745
19. P. Knesl, D. Röseling, and U. Jordis Molecules 11 2006 286
20. P. Ballard, R.H. Bradbury, C.S. Harris, L.F.A. Hennequin, M. Hickinson, J.G. Kettle, J. Kendrew, T. Klinowska, D.J. Ogilvie, S.E. Pearson, E.J. Williams, and I. Wilson Bioorg. Med. Chem. Lett. 16 2006 4908
21. A. Iyobe, M. Uchida, K. Kamata, Y. Hotei, H. Kusama, and H. Harada Chem. Pharm. Bull. 49 2001 822
22. D.M. Jewett Int. J. Radiat. Appl. Instrum. A 43 1992 1383
23. B.H. Mock, G.K. Mulholland, and M.T. Vavrek Nucl. Med. Biol. 26 1999 467
24. M. Wang, M. Gao, B.L. Steele, B.E. Glick-Wilson, C. Brown-Proctor, A. Shekhar, G.D. Hutchins, and Q.-H. Zheng Bioorg. Med. Chem. Lett. 22 2012 4713
25. M. Gao, Z. Shi, M. Wang, and Q.-H. Zheng Bioorg. Med. Chem. Lett. 23 2013 1953
26. M. Wang, M. Gao, and Q.-H. Zheng Bioorg. Med. Chem. Lett. 23 2013 5259
27. M. Gao, M. Wang, B.H. Mock, B.E. Glick-Wilson, K.K. Yoder, G.D. Hutchins, and Q.-H. Zheng Appl. Radiat. Isot. 68 2010 1079
28. M. Wang, M. Gao, K.D. Miller, and Q.-H. Zheng Steroids 76 2011 1331
29. M. Wang, M. Gao, K.D. Miller, G.W. Sledge, and Q.-H. Zheng Bioorg. Med. Chem. Lett. 22 2012 1569
30. M. Allard, E. Fouquet, D. James, and M. Szlosek-Pinaudm Curr. Med. Chem. 15 2008 235
31. M. Gao, M. Wang, G.D. Hutchins, and Q.-H. Zheng Appl. Radiat. Isot. 66 2008 1891
32. B.H. Mock, Q.-H. Zheng, and T.R. DeGrado J. Label. Compd. Radiopharm. 48 2005 S225
33. B.H. Mock, B.E. Glick-Wilson, Q.-H. Zheng, and T.R. DeGrado J. Label. Compd. Radiopharm. 48 2005 S224
34. M. Wang, M. Gao, and Q.-H. Zheng Appl. Radiat. Isot. 70 2012 965
35. M. Gao, M. Wang, K.D. Miller, and Q.-H. Zheng Bioorg. Med. Chem. Lett. 23 2013 4342
36. S.E. Lapi, and M.J. Welch Nucl. Med. Biol. 40 2013 314
37. Q.-H. Zheng, and B.H. Mock Biomed. Chromatogr. 19 2005 671
38. J. DeRuiter, A.N. Brubaker, J. Millen, and T.N. Riley J. Med. Chem. 29 1986 627
39. F.H.S. Curd, J.K. Landquist, and F.L. Ross J. Chem. Soc. 1948 1759